Acetic Anhydride → 2-Acetoxy-4-nitrobenzoic acid

HRID 1959112Notes

Reaction equation

HRID 1959112 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([O:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:16])[CH3:15]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 692664-Nitrosalicylic acid

Product 1

HCID 2959522-Acetoxy-4-nitrobenzoic acid

Procedure

A solution of 2-hydroxy-4-nitrobenzoic acid (16.84 g) in acetic anhydride (60 mL) was heated under reflux overnight. After cooling, the reaction solution was concentrated in vacuo, water and tetrahydrofuran were added to the residue, and the mixture was stirred at room temperature for 4 hours. The aqueous solution was extracted with ethyl acetate, the organic layer was washed successively with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was suspended in diisopropyl ether, the resultant precipitates were collected by filtration and washed with diisopropyl ether to give the titled compound (13.75 g) as a colorless powder.

Workup

  1. temperatureunder reflux overnight
  2. temperatureAfter cooling
  3. concentrationthe reaction solution was concentrated in vacuo, water and tetrahydrofuran
  4. additionwere added to the residue
  5. extractionThe aqueous solution was extracted with ethyl acetate
  6. washthe organic layer was washed successively with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customthe resultant precipitates
  10. filtrationwere collected by filtration
  11. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-ba620bf2e0af408c88dff229b26b1275
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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